Sleepless Nights
by Monroe-Militia
Summary: Charlie is working for the rebels and poses as a prostitute in order to get into bed with the leader of the Monroe Republic's son. If she can get close to Monroe's son, then maybe she can get close to whatever he's planning as well. But when Connor starts to fall for her she has more to worry about than just getting caught. Will she be able to prevent falling for him? Slight AU
1. Chapter 1

"Absolutely not," Miles told his niece in a stern tone.

"Charlie, don't." Rachel added just as sternly before her voice cracked a little. "_Please_ don't."

"Come on, this chance isn't just going to present itself again," Charlie pointed out. "It's a good plan. When else are we going to get a chance to get into Monroe's headquarters to try and figure out what he's planning and take him down from the inside?"

"If you get caught, you'll be dead," Rachel pointed out. "And that's if you're lucky."

"…I'll do it," Nora piped up.

"You have a tattoo of an American flag," Charlie pointed out. "That's a dead give-away that you're a rebel… I can do it. I'll be fine… Really."

"I am not going to let my daughter go hand herself over as whore to Monroe's son," Rachel argued. "You don't have to do this, Charlie."

"It's not your choice to let me or not," Charlie responded. "And I do have to. Whatever Monroe's planning isn't good. And if sleeping with his son means that we might be able to stop him and save who knows how many lives then it's worth it."

Rachel looked sick as she told her daughter, "At least be careful."

"I will be," Charlie responded. She knew that the words were empty, but figured they might be enough to at least comfort her mother a little.

"If you're going in there, then you're going to need something else to wear," Nora pointed out. "You are way too covered to fit in inside a whore house."

Charlie knew that Nora was probably right and looked around to search for a solution. She noticed that a couple of the workers were outside, leaning against the building and chatting.

"I have an idea," she said before turning and walking over to the two women.

"How much for your dress?" She questioned one of them.

"Honey, clothes ain't what I'm selling," the prostitute responded, causing the other to start snickering.

"Is this enough?" Charlie asked insistently.

The whore looked like she had been about to roll her eyes when she spotted the handful of diamonds that Charlie was offering over to her and hesitated.

"And you can have my clothes," Charlie added hopefully.

* * *

A few minutes later, Charlie stood in front of the entrance to the whorehouse dressed in a skimpy dress and heels that she could barely walk in.

"Your mom is right you know," Nora told her. "You don't have to do this."

The others didn't want to blow Charlie's cover, so they were already getting ready to go back to rebel headquarters. That meant it was just her and Nora.

"Yes. I do." Charlie said seriously before she managed to crack the slightest of smiles. "But at least he's cute, right? I mean, as cute as an evil dictator's son can really be…"

Nora smiled back at her. "Good luck."

"I'll be fine," Charlie insisted one more time before she took in a deep breath and stepped inside.

She immediately spotted him, standing by the bar with a drink in his hand and a grin on his lips. He was utterly surrounded by girls. He must be a hot commodity. Monroe's son probably paid a lot better than any of them were used to getting.

Charlie still had no idea how exactly she was going to convince him to take her home, even if she could get to him, so she decided to head over to the opposite side of the bar first to get a drink as she tried to get her nerve up and figure out what she was going to do.

When she'd finished her drink she decided that, plan or not, she still needed to act now. She couldn't go back and tell everyone that she had let him walk out with someone else without even trying.

She turned to get off of her stool and found herself staring into the eyes of Connor Monroe himself. He was already walking her way with a tilted smile on his lips.

He sat down beside her and then grinned as many of the women glared over at her, already jealous of the tiny bit of attention she was getting.

"All the other girls in here are throwing themselves at me," he commented. "But not you… Why?"

Great, she'd already blown her cover. A+ job, Charlie…

"I'm new here," she told him, struggling to hold on to any chance of remaining undercover. "I'm not used to all of the competition."

"Hmmm, I bet you're not," he agreed, looking her up and down ever so slowly with a smile still tugging at his lips. His eyes remained on her chest where the dress dipped down low in the front for several long seconds before they finally flicked back up to meet her eyes.

Okay, maybe her cover was still intact…

"And I'm sure that you're more than used to all of this fighting over you," Charlie told him in her most flirtatious tone as she placed her elbow on the bar-top and moved to lean her head on her hand, letting her chest stick forward a little more than usual. "Especially with a face like that."

The corner of her lip twitched upwards when he immediately took the bait and looked back down at her cleavage again.

She knew by his inability to think of a response that she had him drawn in and it was time to kick things up a notch. She leaned over, splitting the distance between them in half as one hand moved to his bicep.

His gaze turned to her hand on his arm and her lips were hovering just inches away from his as she added on, "Especially with a body like that…"

As her hot breath hit his lips, his eyes flickered back up to hers.

"I'm Charlie, by the way," she told him with a seductive smile as her hand slid down from his arm to his inner thigh.

"Well, Charlie," he said with a wide smirk. "What do you say we get out of here?"

"I'd love to."

* * *

Charlie had to suppress a grin when, not too long afterwards, she was being led through the front entrance of Monroe's headquarters and straight past the armed guards.

Once they had gotten inside and a little down the hallway, Connor looked back over his shoulder at her, blatantly staring at her in a way that would usually cause her to hand out a few good death threats. But not this time, instead she shot him her flirtiest smile.

It must have worked because he stopped and turned to stare at her with his undivided attention.

She took the opportunity to close the distance between them, pulling him closer by the collar of his shirt until her lips were on his. One of her hands tangled into the curls of his hair as the other still rested on his chest.

He pulled her closer to him with one warm hand on her hip and the other on the small of her back. As the kiss deepened, his second hand slid down to grab her backside.

She forced out a small giggle of surprise against his lips in response. She could feel him pressing against her upper thigh through his pants, so she slid her hand ever so slowly down from his chest to grab him through the fabric.

As he let out a moan against her lips she thought to herself that this was almost too easy.

He reluctantly pulled away from her to continue leading her down the hallway and Charlie silently cursed at herself for jinxing things when she noticed the pair of guards at the end of the hall, one of whom was smirking over at them.

He led her around a turn and as she looked down the other hallways she discovered that there were guards everywhere.

When they reached Connor's room a pair of guards was stationed outside the door. If the place was this protected where she'd seen, then she couldn't imagine how difficult it was going to be trying to get into Monroe's office.

She had definitely jinxed herself by thinking this was easy.

As Connor pulled her through the door and towards him, she forced any thoughts of trying to get into that office out of her mind as she forced her whole concentration back onto Connor and making him happy enough that he'd want to keep her around for a while.

* * *

**A/N: Please read and review! :) I hope you guys liked the chapter. This idea just came to me today and I couldn't get rid of it.  
**


	2. Chapter 2

When Charlie woke up the next morning, she found that Connor was already awake and sitting up. She wasn't exactly sure what the protocol here was, but she figured just getting dressed and leaving would be a safe bet.

…There was only one problem with that. Connor had ripped her dress in half the night before. She had nothing to wear out of here and she was sure that her mom and Miles would flip if she came back without a scrap of clothing on.

"I have to go," she said as she rolled on her side to face him. "And something tells me that dress is no longer wearable."

"Well then maybe you should just stay here and wear nothing," he suggested with a grin.

"Cute, but we both know that you have more important things to do with your day," she pointed out with a teasing smile. "You won't even notice that I'm gone until tonight... And I could be tempted to come back. For a price."

Connor let out a small laugh at that.

"You should definitely come back," he told her.

"You'd have to find me something to wear on the way out first," she teased. "I'm sure that somewhere in this place there's a spare set of clothes."

She knew that ordering him around could end up being a bad choice, but she thought that she could afford to push her luck a little.

"I guess it is my responsibility to go find you a dress," he commented. "Since I'm the one who wrecked the first one… I'll be back in a second."

He got up and pulled on the bare minimum amount of clothing before leaving the room.

Charlie let her head fall back onto the pillow as she silently hoped that he really would come back with clothes instead of just leaving her there all day.

She decided that there were better uses of her time unsupervised in his room, so she sat up and eyed the rest of the room. She quickly scanned to see if anything popped out at her as possibly being important, but all that she saw was a whole lot of nothing. That wasn't overly surprising… Why would he leave anything important in here if he was going to have total strangers spend the night?

She was about to get up to search a little more thoroughly when the sound of the door opening caused her head to whip around.

Connor tossed a new dress, at least as revealing as the one that she had shown up in the night before, and a pouch of diamonds over to her before he turned towards his dresser to go grab some clothes without a glance back at her.

* * *

"You are _not_ going back there," Rachel insisted.

"I have to," Charlie argued.

"You said yourself that there were guards everywhere," Rachel pointed out. "Even if you could take a few of them out, new ones would hear you and come to take their place. How do you think that you're going to get anywhere near something important?"

"I'll figure it out," her daughter responded angrily. "I've gotten closer than anybody else has. And if I go back then I can get more information to use to plan out how I'm going to do it."

Nora walked in the room then and Charlie tossed the pouch that Connor had given her over.

"Here, some new funding," Charlie told her. "Courtesy of mini Monroe."

Nora opened the pouch and looked inside, seeming impressed. "You must have given him quite the night."

Charlie let out a laugh before she asked, "Could you imagine the look on Monroe's face if he found out that his son was inadvertently funding the rebellion?"

"It's not funny, Charlie," Rachel argued. "If Monroe finds out, he'll make an example out of you."

"Well then I guess that it's a good thing that he isn't going to find out," Charlie told her.

"Did you find anything out?" Nora questioned.

"Not yet," Charlie responded. "I'm going back tonight though."

"Have I mentioned that I hate this plan lately?" Danny questioned. "Seriously, I stay home for one night and you start whoring yourself out to a Monroe."

"You've already complained about this four hundred times in the last ten minutes," his sister replied. "And I'm still not changing my mind about this. I didn't screw him last night so that I could back out now."

* * *

When Charlie returned to Monroe's headquarters, the guards immediately let her through and each one that she passed told her which way to turn to get to Connor's room. It was an advantage to be able to get past some of the guards, but she wasn't sure how she felt about them giving her directions. It was going to be hard to wander off anywhere else.

Connor wasn't back yet when Charlie entered his room, so she decided to take the chance to rummage through his stuff a little.

As she searched through things, she was careful that she didn't move them too far. She listened carefully for the sound of footsteps outside the door and made sure that at any given point that she wouldn't have too many things out of place to fix. She needed be able to put everything back in place before he could get through the door.

She managed to check the whole room to no avail. She'd been expecting this result, but still had figured that it was worth a try to check.

Connor still wasn't back, so Charlie took a seat on his bed to wait. As she did, she considered what she should do when he came in to try and keep her cover.

By the time that the door actually moved, Charlie had settled on the one-liner, 'See, it's like I never even left', but she didn't get the chance to say it.

She only managed to get a word or two out before Connor had already closed the distance between them, wasting no time before kissing her hard.

She supposed that she shouldn't really be surprised. After all, he wasn't paying her for talk.

* * *

**A/N: please read and review! A special thanks goes out to Sexy Meat Pies, bbp23, and Loveforthestory for reviewing the first chapter :)**


	3. Chapter 3

Charlie had spent every night with Connor for the last week, but she still didn't have any idea of how she was going to get into Monroe's office. She had, however, overheard a couple of guards gossiping and found out that Monroe had left and taken a couple of his best men with him on some important trip. That didn't sound good and she knew that she needed to figure out some sort of plan by the time that he got back, unless she wanted it to already be too late.

"I feel sorry for you," Nora commented as she and Charlie lounged around in rebel headquarters. "…Having to sleep with mini Monroe, especially when he thinks you're a whore… I mean it's got to be all about him, right?"

"I so don't want to hear about this," Danny complained as he got up and left the room, taking Miles' precious whiskey with him.

Nora snickered a little as she watched him go.

Once it was just the two of them, Charlie asked her, "Can we not call him mini Monroe?"

"Mini Monroe was your nickname for him, remember?" The older woman pointed out.

"Yeah, but now it grosses me out," Charlie responded. "I prefer not to think about the fact that he's related to Monroe when I'm sleeping with him."

"I could understand that," Nora agreed. "But you still haven't answered me. It's all about him in the bedroom, isn't it?"

"He's not that bad… I mean maybe it was all about him the first couple of nights, but now I've got him wrapped around my finger," Charlie responded.

"Are you kidding me?" Nora questioned. "Okay, but he still must suck in bed... He must have like no practice actually trying to pleasure someone else, right? And even if he has had practice, it must have been with whores who would tell him he was amazing no matter what, right?"

Charlie let out a small laugh, "Well, actually…"

"Seriously? How in the hell did you end up getting paid to get good sex?" Nora demanded. "I mean I know it's with an evil dictator's son, so that's kind of a drag, but you said it yourself that he's pretty cute."

"It's not like I'm only there to sleep with him," Charlie pointed out. "I still have to figure out how the hell I'm going to get near anything important."

"Yeah, and I'm sure that you aren't even enjoying yourself a little bit in the meantime," Nora retorted sarcastically.

* * *

As soon as Connor walked into his room, Charlie headed towards him to take charge from the start.

A grin formed on his lips at the sight of her. But as he opened his mouth to speak, he instead found her tongue in his mouth.

As they kissed, she dragged him over to the bed and then pushed him back onto it.

"Someone's eager," he commented with a grin as she crawled onto the bed and began to kiss at his neck.

She let out a small laugh against his skin before ripping the front of his shirt open, sending buttons flying everywhere.

"I know that it's my responsibility to find you a new shirt, since I wrecked this one," Charlie purred in his ear. "But I like you so much better out of it."

"Well then maybe I shouldn't have gotten you that dress," Connor told her. He let out a chuckle as he grabbed her by the hips and rolled them over. "Since I certainly prefer you out of it."

Charlie smirked a little before bringing her lips back to his and rolling them over again so that she was back on top, sitting on his chest to keep him from trying that again.

As she grabbed his hands and pinned them above his head, he grinned up at her and commented, "You're something else, Charlie."

Most girls would never risk trying to take charge with him. Usually he would hate it, but there was something about the way that Charlie did it that he couldn't resist.

"But in all the best ways, right?" She asked in her most flirtatious tone. "…You know you love it."

With that she brought her lips back down to meet his.

A few minutes later, when she came up for air, Connor told her, "You know, you're completely ruining other girls for me."

"Good," she told him with a wide grin.

* * *

Charlie had stayed there overnight each time so far, but she couldn't quite make herself do it this time… He just looked so innocent and vulnerable as he slept and it was making the guilt that much worse.

In normal life, she definitely didn't sleep around. She'd never slept with a guy right off the bat like this before. She'd always been overly cautious and had gotten to know guys well before jumping into bed with them.

Sex meant something to her, but she was pushing that aside for this whole mission. At first it hadn't been that hard because she had known that it meant nothing to him. But now it seemed like Connor was starting to get attached and, although she knew that it was a good thing as far as the mission went, that didn't help get rid of the pit of guilt in her gut.

She had been lying awake for what felt like hours on end when she finally slipped carefully from the bed and pulled her dress back on before tiptoeing towards the doorway, carrying her shoes with her so that they wouldn't make any noise.

As she walked down the halls and out of the front door, she ignored the looks from all of the guards that she passed. She had become more than used to the walk of shame during the last week, although she was used to doing it in the morning instead of the dead of night.

* * *

By the time that she got back to rebel headquarters, everyone was already off to bed. She crept carefully down the hallways and towards her room.

She couldn't stand the idea of waking anyone up right now and having to deal with their questions about what she was doing back already.

She turned into her room and crawled into her own bed, which had remained untouched for days, to try to get some sleep. Despite her best efforts, sleep didn't come until almost the crack of dawn.

* * *

**A/N: Please read and review! Also a huge thanks goes out to these incredible people for reviewing the second chapter: Sexy Meat Pies, bbp23, and Loveforthestory :) **


	4. Chapter 4

Luckily for Charlie, no one in rebel headquarters seemed to have noticed that she had come back early the night before. Or if they did, they at least didn't mention it to her which was a relief within itself.

Unfortunately, when it came time for her nightly visit to Connor, Charlie was still exhausted and sleep-deprived from the night before.

Once again, Charlie found herself alone in Connor's room as she waited for him to get back.

This time she decided to lie down as she waited, figuring that she may as well make herself comfortable as she waited.

Connor was later than usual and after an hour of waiting for him, Charlie drifted off to sleep.

* * *

By the time that Connor finally headed back to his room, he was beyond exhausted from the long day he'd had. As he walked through the hallways, he wondered to himself whether Charlie would be back again or not.

She had disappeared in the middle of the night before and he had woken up to find her missing for the first time since he had met her. He wasn't sure of why she had snuck out or what it had meant, but he did know that he had been surprisingly disappointed to find that she was gone.

As Connor walked through the doorway of his room, he smiled to himself at what he found.

There she was, lying curled up on top of the covers and fast asleep. He must really be back late then.

Connor approached the bed slowly, trying to remain as quiet as possible, before stopping next to Charlie, who had goose bumps standing out on the flesh of her arms.

He brushed a loose strand of hair that had fallen over her face out of the way before he carefully bent down to lift her up, being careful not to wake her as he did so.

Once she was in his arms, he shifted so that he held her against his chest with one arm as his other pulled the covers back. He then gently placed her back down on the bed, setting her head down on the pillow, before pulling the covers back up to tuck her in.

He walked around the bed and sat down on the other side, then kicked his shoes off before reaching to unfasten the buttons on his shirt.

Once he had stripped off enough clothes to be suitably dressed for sleeping, Connor pressed his lips to Charlie's forehead before crawling into bed to get some much needed sleep himself.

* * *

When Charlie woke up the next morning, she was first surprised to find that she had fallen asleep while waiting. Next, she was surprised when she realized that it was already light out. That meant that it was morning and Connor must have already come back.

Charlie blinked a few times to try and wake up a little more before she moved to sit up, only to find a whole new set of surprises.

Connor was nowhere to be seen, but she now realized that she was under the covers which she was certain she had been waiting lying on top of.

Charlie looked down at the bed in confusion and that's when she spotted it out of the corner of her eye.

There, sitting on top of Connor's pillow, was a folded up piece of paper that was being held down by two pouches of diamonds.

Charlie understood that one of them was for the night that she had left while he was asleep without having been paid yet. What she didn't understand was why she seemed to be getting paid for falling asleep. She also didn't particularly understand why Connor hadn't just woke her up when he had gotten back.

She slowly moved the pouches out of the way before hesitantly picking up the piece of paper. She was dreading finding out what was written on it.

_You were asleep when I got here and looked like you could use the rest. I didn't want to wake you. See you tonight._

Charlie felt a surge of anger as she balled her hand into a fist, crumpling the note within it.

This was not how things were supposed to go... Charlie was supposed to be just a whore to Connor, nothing more… He wasn't supposed to be letting her sleep or tucking her in or leaving her notes on his pillow when she was still sleeping as he left.

Why did he have to make everything so much more complicated for her? She already had enough to worry about without this.

* * *

"Here's the pay for the last couple of nights," Charlie commented as she handed the pouches of diamonds over to Nora.

Nora could sense that there was something off with the other woman, but she couldn't put her finger on what exactly that something was.

"You alright, Charlie?" She asked.

"Yeah, I'm fine," Charlie told her.

"Are you sure?" Nora checked.

"Positive," Charlie lied.

* * *

Charlie felt an ever-growing pit of dread in her gut as she waited in Connor's room.

This time, she didn't have to wait long, since he arrived at the door mere minutes after she had.

She definitely was not in any mood for talking, so she decided to try and prevent any attempts on his behalf by sliding her dress off of her shoulders and letting it fall to the floor.

It wasn't anything that Connor hadn't seen before, yet a huge grin still formed on his lips as she did so.

Charlie closed the distance between them and wrapped her arms around his neck as she brought her lips to his, mostly just so that she wouldn't have to see him looking at her like that anymore. Charlie's guilt was at an all-time high, but she had a job to do and she couldn't let that show.

Connor grabbed her by the legs to lift her up and Charlie's legs instinctively wrapped around his waist. She forced herself to smile against his lips at that as she tightened her arms around him even further, pulling herself as close to him as possible.

* * *

"Where are you going?" Connor questioned as Charlie got out of bed.

Charlie forced herself to smile over at him as she teased, "Wouldn't you like to know?"

"You should stay over tonight," he commented as he watched her grab her clothes up off of the floor. "I missed you the other night."

"You were asleep when I left," Charlie pointed out as she got began to get dressed. "You didn't even notice that I was gone until morning."

"I like waking up with you here," he admitted with a gut-wrenching smile.

"I'm not your girlfriend, Connor," Charlie insisted while keeping her tone as playful as possible. She knew she was walking a very thin line here. "And I don't do the girlfriend experience. My job here's done for the night."

She saw his face fall and quickly turned away. That was something she couldn't stand to watch right then, so instead she just headed for the door without waiting for his response.

* * *

**A/N: Please read and review! A giant thanks goes out micha, bbp23, Loveforthestory, rita, and Procrastinatinggenius for leaving reviews on last chapter! :)  
**


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